Salicylaldehyde → 2-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carbothioamide

HRID 867908Notes

Reaction equation

HRID 867908 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[OH-].[Na+].[OH:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O.[CH3:17][N:18]=[C:19]=[S:20]>C(O)C>[CH3:17][NH:18][C:19]([N:2]1[CH2:3][CH2:4][S:5][CH:11]1[C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[OH:8])=[S:20]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 9082Cysteamine HydrochlorideHCID 11167Methyl isothiocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 137495312-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carbothioamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of cysteamine hydrochloride (11.3 g) in ethanol (250 ml) is added sodium hydroxide (4.0 g), and the mixture is stirred for 30 minutes under argon gas. A solution of 2-hydroxybenzaldehyde (12.2 g) in ethanol (40 ml) is added to the mixture, and the mixture is refluxed for 4 hours. To the mixture is added methyl isothiocyanate (7.9 g), and the mixture is further refluxed for 4 hours. After distilling off the solvent under reduced pressure, a mixture of water and ethanol is added to the resulting residue, and the insoluble crystals are collected by filtration. The crystals thus obtained are washed with water and ethanol and recrystallized from ethanol to give N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carbothioamide (7.9 g, yield: 31.1%).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperaturethe mixture is further refluxed for 4 hours
  3. distillationAfter distilling off the solvent under reduced pressure
  4. additiona mixture of water and ethanol
  5. additionis added to the resulting residue
  6. filtrationthe insoluble crystals are collected by filtration
  7. customThe crystals thus obtained
  8. washare washed with water and ethanol
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3273182fbd5147bfa9a3a0085a757f01
Source dataset
uspto-grants-1988_10
Patent number
US04777178

Reaction notes

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